JP5475284B2 - 親水性架橋ポリマー - Google Patents

親水性架橋ポリマー Download PDF

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Publication number: JP5475284B2
Authority: JP; Japan
Prior art keywords: alkyl; polymer; group; atoms; substituted
Prior art date: 2005-08-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

JP2008524371A

Other languages

English (en)

Japanese (ja)

Other versions

JP2009503203A (ja

Inventor

イェンック，マティアス

ザブロウスキー，エックハルト

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Merck Patent GmbH

Original Assignee

Merck Patent GmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2005-08-03

Filing date

2006-06-08

Publication date

2014-04-16

2005-08-03 Priority claimed from EP05016846A external-priority patent/EP1754534A1/fr

2006-06-08 Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH

2009-01-29 Publication of JP2009503203A publication Critical patent/JP2009503203A/ja

2014-04-16 Application granted granted Critical

2014-04-16 Publication of JP5475284B2 publication Critical patent/JP5475284B2/ja

Status Active legal-status Critical Current

2026-06-08 Anticipated expiration legal-status Critical

Links

229920006037 cross link polymer Polymers 0.000 title description 8
-1 substituted alkyl vinyl ether Chemical compound 0.000 claims description 128
229920000642 polymer Polymers 0.000 claims description 87
125000000217 alkyl group Chemical group 0.000 claims description 62
238000000926 separation method Methods 0.000 claims description 40
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
239000000463 material Substances 0.000 claims description 35
229910052760 oxygen Inorganic materials 0.000 claims description 34
239000012636 effector Substances 0.000 claims description 30
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 28
150000003254 radicals Chemical class 0.000 claims description 26
239000000178 monomer Substances 0.000 claims description 25
239000003463 adsorbent Substances 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 24
125000001424 substituent group Chemical group 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
239000002245 particle Substances 0.000 claims description 19
238000010557 suspension polymerization reaction Methods 0.000 claims description 19
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
229910052717 sulfur Inorganic materials 0.000 claims description 18
229910005965 SO 2 Inorganic materials 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
238000006116 polymerization reaction Methods 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
238000004587 chromatography analysis Methods 0.000 claims description 14
229920001577 copolymer Polymers 0.000 claims description 13
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 12
125000000172 C5-C10 aryl group Chemical group 0.000 claims description 12
239000011148 porous material Substances 0.000 claims description 12
239000003431 cross linking reagent Substances 0.000 claims description 11
238000010559 graft polymerization reaction Methods 0.000 claims description 9
239000003381 stabilizer Substances 0.000 claims description 9
239000004971 Cross linker Substances 0.000 claims description 6
239000003361 porogen Substances 0.000 claims description 6
239000000725 suspension Substances 0.000 claims description 6
WULAHPYSGCVQHM-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethanol Chemical compound OCCOCCOC=C WULAHPYSGCVQHM-UHFFFAOYSA-N 0.000 claims description 5
HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 claims description 5
MOOIXEMFUKBQLJ-UHFFFAOYSA-N [1-(ethenoxymethyl)cyclohexyl]methanol Chemical compound C=COCC1(CO)CCCCC1 MOOIXEMFUKBQLJ-UHFFFAOYSA-N 0.000 claims description 5
238000010532 solid phase synthesis reaction Methods 0.000 claims description 5
BCTDCDYHRUIHSF-UHFFFAOYSA-N 5-ethenoxypentan-1-ol Chemical compound OCCCCCOC=C BCTDCDYHRUIHSF-UHFFFAOYSA-N 0.000 claims description 4
239000013543 active substance Substances 0.000 claims description 4
HMYBDZFSXBJDGL-UHFFFAOYSA-N 1,3-bis(ethenyl)imidazolidin-2-one Chemical compound C=CN1CCN(C=C)C1=O HMYBDZFSXBJDGL-UHFFFAOYSA-N 0.000 claims description 3
VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 claims description 3
OJXVWULQHYTXRF-UHFFFAOYSA-N 3-ethenoxypropan-1-ol Chemical compound OCCCOC=C OJXVWULQHYTXRF-UHFFFAOYSA-N 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 3
238000006555 catalytic reaction Methods 0.000 claims description 3
ITZXULOAYIAYNU-UHFFFAOYSA-N cerium(4+) Chemical compound [Ce+4] ITZXULOAYIAYNU-UHFFFAOYSA-N 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
JVGOEGSMSPAINF-UHFFFAOYSA-N 1,3-bis(ethenyl)-1,3-diazinan-2-one Chemical compound C=CN1CCCN(C=C)C1=O JVGOEGSMSPAINF-UHFFFAOYSA-N 0.000 claims description 2
238000002955 isolation Methods 0.000 description 19
125000003118 aryl group Chemical group 0.000 description 18
150000001875 compounds Chemical class 0.000 description 16
239000000203 mixture Substances 0.000 description 16
239000012071 phase Substances 0.000 description 16
229910052757 nitrogen Inorganic materials 0.000 description 14
239000000758 substrate Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
102000004169 proteins and genes Human genes 0.000 description 13
108090000623 proteins and genes Proteins 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
125000002723 alicyclic group Chemical group 0.000 description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
239000000243 solution Substances 0.000 description 11
125000001072 heteroaryl group Chemical group 0.000 description 10
125000003545 alkoxy group Chemical group 0.000 description 8
230000027455 binding Effects 0.000 description 8
239000003446 ligand Substances 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
239000003921 oil Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
238000001542 size-exclusion chromatography Methods 0.000 description 7
239000002904 solvent Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000003999 initiator Substances 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
FPSURBCYSCOZSE-UHFFFAOYSA-N 1-ethenoxybutan-1-ol Chemical compound CCCC(O)OC=C FPSURBCYSCOZSE-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
229920001222 biopolymer Polymers 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
229920001477 hydrophilic polymer Polymers 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
125000000547 substituted alkyl group Chemical group 0.000 description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
239000008186 active pharmaceutical agent Substances 0.000 description 4
125000004183 alkoxy alkyl group Chemical group 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
125000004181 carboxyalkyl group Chemical group 0.000 description 4
238000007334 copolymerization reaction Methods 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
125000004966 cyanoalkyl group Chemical group 0.000 description 4
238000009826 distribution Methods 0.000 description 4
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
239000011159 matrix material Substances 0.000 description 4
238000005259 measurement Methods 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
102000004196 processed proteins & peptides Human genes 0.000 description 4
108090000765 processed proteins & peptides Proteins 0.000 description 4
125000004963 sulfonylalkyl group Chemical group 0.000 description 4
239000004094 surface-active agent Chemical class 0.000 description 4
230000008961 swelling Effects 0.000 description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
108020004414 DNA Proteins 0.000 description 3
229920002307 Dextran Polymers 0.000 description 3
YCZVNBQAIZENBU-UHFFFAOYSA-N NC(=O)N.C(=C)C=CC=C Chemical compound NC(=O)N.C(=C)C=CC=C YCZVNBQAIZENBU-UHFFFAOYSA-N 0.000 description 3
239000004372 Polyvinyl alcohol Substances 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001212 derivatisation Methods 0.000 description 3
125000004663 dialkyl amino group Chemical group 0.000 description 3
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
238000010828 elution Methods 0.000 description 3
125000003700 epoxy group Chemical group 0.000 description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
125000005647 linker group Chemical group 0.000 description 3
238000012434 mixed-mode chromatography Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000007523 nucleic acids Chemical class 0.000 description 3
108020004707 nucleic acids Proteins 0.000 description 3
102000039446 nucleic acids Human genes 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000005192 partition Methods 0.000 description 3
229920002451 polyvinyl alcohol Polymers 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000001179 sorption measurement Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000005208 trialkylammonium group Chemical group 0.000 description 3
YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 2
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
125000005916 2-methylpentyl group Chemical group 0.000 description 2
125000005917 3-methylpentyl group Chemical group 0.000 description 2
ASPUDHDPXIBNAP-UHFFFAOYSA-N 6-ethenoxyhexan-1-ol Chemical compound OCCCCCCOC=C ASPUDHDPXIBNAP-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
102000053602 DNA Human genes 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
102000016943 Muramidase Human genes 0.000 description 2
108010014251 Muramidase Proteins 0.000 description 2
108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
125000005037 alkyl phenyl group Chemical group 0.000 description 2
125000004103 aminoalkyl group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000002902 bimodal effect Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
238000010538 cationic polymerization reaction Methods 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000011437 continuous method Methods 0.000 description 2
239000012228 culture supernatant Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
125000004985 dialkyl amino alkyl group Chemical group 0.000 description 2
238000007720 emulsion polymerization reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000011521 glass Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
125000001165 hydrophobic group Chemical group 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
150000002484 inorganic compounds Chemical class 0.000 description 2
229910010272 inorganic material Inorganic materials 0.000 description 2
230000003993 interaction Effects 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000002502 liposome Substances 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
230000010874 maintenance of protein location Effects 0.000 description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
125000003884 phenylalkyl group Chemical group 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229920001289 polyvinyl ether Polymers 0.000 description 2
230000001376 precipitating effect Effects 0.000 description 2
238000004237 preparative chromatography Methods 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000005855 radiation Effects 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
230000003068 static effect Effects 0.000 description 2
238000001256 steam distillation Methods 0.000 description 2
238000003860 storage Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
ZICNIEOYWVIEQJ-UHFFFAOYSA-N (2-methylbenzoyl) 2-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1C ZICNIEOYWVIEQJ-UHFFFAOYSA-N 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
229940043375 1,5-pentanediol Drugs 0.000 description 1
UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 1
XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
RUKCSZJSODAPHD-UHFFFAOYSA-N 3-ethenylpenta-1,3-diene Chemical group CC=C(C=C)C=C RUKCSZJSODAPHD-UHFFFAOYSA-N 0.000 description 1
LNYTUARMNSFFBE-UHFFFAOYSA-N 4-(diethylazaniumyl)benzoate Chemical compound CCN(CC)C1=CC=C(C(O)=O)C=C1 LNYTUARMNSFFBE-UHFFFAOYSA-N 0.000 description 1
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
HAZOOPRJJXBTJF-UHFFFAOYSA-N C(=C)N1C(N(CCC1)C=C)=O.NC(=O)N.C(=C)C(=CC)C=C Chemical compound C(=C)N1C(N(CCC1)C=C)=O.NC(=O)N.C(=C)C(=CC)C=C HAZOOPRJJXBTJF-UHFFFAOYSA-N 0.000 description 1
0 C*C(NC)=C(*)O*C Chemical compound C*C(NC)=C(*)O*C 0.000 description 1
125000005915 C6-C14 aryl group Chemical group 0.000 description 1
150000000703 Cerium Chemical class 0.000 description 1
108010038061 Chymotrypsinogen Proteins 0.000 description 1
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
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- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/282—Porous sorbents
- B01J20/285—Porous sorbents based on polymers
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F216/14—Monomers containing only one unsaturated aliphatic radical
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F261/00—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00
- C08F261/06—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated ethers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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- Y10T428/00—Stock material or miscellaneous articles
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Polymers & Plastics (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Graft Or Block Polymers (AREA)
Treatment Of Liquids With Adsorbents In General (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
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JP2008524371A 2005-08-03 2006-06-08 親水性架橋ポリマー Active JP5475284B2 (ja)

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Application Number	Priority Date	Filing Date	Title
EP05016846A EP1754534A1 (fr)	2005-08-03	2005-08-03	Polymère hydrophile réticulé
EP05016846.7		2005-08-03
EPPCT/EP2006/005296		2006-06-02
EPPCT/EP2006/005296		2006-06-02
PCT/EP2006/005484 WO2007014591A1 (fr)	2005-08-03	2006-06-08	Polymere reticule hydrophile

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JP5475284B2 true JP5475284B2 (ja)	2014-04-16

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US (3)	US7951885B2 (fr)
EP (1)	EP1910433B1 (fr)
JP (1)	JP5475284B2 (fr)
KR (1)	KR101289911B1 (fr)
CN (2)	CN102417557B (fr)
CA (1)	CA2617645C (fr)
ES (1)	ES2528426T3 (fr)
WO (1)	WO2007014591A1 (fr)

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CA2617645C (fr) *	2005-08-03	2014-09-09	Merck Patent Gesellschaft Mit Beschraenkter Haftung	Polymere reticule hydrophile
CA2655873C (fr)	2006-07-14	2017-10-17	Wisconsin Alumni Research Foundation	Membranes adsorbantes pour pieger des virus
JP5631869B2 (ja) *	2008-05-30	2014-11-26	メルクパテントゲゼルシャフトミットベシュレンクテルハフツングＭｅｒｃｋＰａｔｅｎｔＧｅｓｅｌｌｓｃｈａｆｔｍｉｔｂｅｓｃｈｒａｅｎｋｔｅｒＨａｆｔｕｎｇ	水酸基を含まないポリマー上におけるＣｅ（ＩＶ）で開始されるグラフト重合
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CN102417557B (zh)	2015-03-11
KR20080039472A (ko)	2008-05-07
EP1910433B1 (fr)	2014-11-05
WO2007014591A1 (fr)	2007-02-08
CN101258175B (zh)	2011-11-16
US20080210615A1 (en)	2008-09-04
US7951885B2 (en)	2011-05-31
CA2617645C (fr)	2014-09-09
CN101258175A (zh)	2008-09-03
KR101289911B1 (ko)	2013-07-26
EP1910433A1 (fr)	2008-04-16
CN102417557A (zh)	2012-04-18
US20110091727A1 (en)	2011-04-21
ES2528426T3 (es)	2015-02-09
US20140155565A1 (en)	2014-06-05
US8765897B2 (en)	2014-07-01
CA2617645A1 (fr)	2007-02-08
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